"Crooked Smile" is a song by American hip hop recording artist and record producer J. Cole, released June 4, 2013, as the second official single from his second studio album, Born Sinner (2013). The song was produced by Cole himself, and Elite. The song samples Jennifer Hudson's "No One Gonna Love You" and features guest vocals from R&B group TLC. The song has since peaked at number 27 on the US Billboard Hot 100 chart.

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The single features the R&B group TLC who had not released a new single in over seven years since the release of their single "I Bet (feat. O'so Krispie)", which was released in 2005 as part of the digital version of their compilation Now and Forever: The Hits,[1] and as a promotional cut from their reality series R U the Girl. An editor from Billboard commented on the song saying: "The Born Sinner track is an uplifting ode to all those who continue to hold their heads up, especially women, and the importance of inner beauty."[2] The original version of Crooked Smile was released January 28, 2014 on Dreamville's compilation mixtape titled Revenge of the Dreamers, the song samples "Str8 Ballin'" by 2Pac.[3]

After Cole and TLC had teased the music video for over a month, on September 18, 2013 the video was released.[4] TLC does not appear in the video with J. Cole but their verses are featured. It is dedicated to Aiyana Stanley-Jones.